The stereospecific preparation of (E)-1,2-difluoro-1,2-disubstituted alkenes

被引：1
|
作者：
Lu, Long [1 ]
Burton, Donald J. [1 ]
机构：
[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA
来源：
JOURNAL OF FLUORINE CHEMISTRY | 2012年 / 143卷
关键词：
Palladium catalysis; Silicon/stannane exchange; Cu(I)I co-catalysis; Aryl iodides; (E)-1,2-difluoroalkenes; (E)-2,3-DIFLUORO-3-STANNYLACRYLIC ESTER; STEREOSELECTIVE PREPARATION; REAGENTS; ROUTE;
D O I：
10.1016/j.jfluchem.2012.02.010
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
(Z)-1,2-difluoro-2-substituted vinyl silanes were prepared stereospecifically from chlorotrifluoroethene, chlorotrimethylsilane and alkyl or aryllithium reagents. Subsequent exchange of the trimethylsilyl group via reaction of the vinylsilane with KF/n-Bu3SnCl/DMF stereospecifically afforded the corresponding (Z)-1,2-difluoro-2-substituted vinyl stannanes. Pd(PPh3)(4)/Cu(I)I/DMF coupling of the vinyl stannanes with substituted aromatic iodides stereospecifically provided the (E)-1,2-difluoro-1-substituted aryl-alkenes in excellent yield. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码：94 / 98
页数：5
相关论文
共 50 条
  • [31] A convenient synthesis of 1,2-disubstituted cyclooctatetraenes
    Rigby, JH
    Warshakoon, NC
    TETRAHEDRON LETTERS, 1997, 38 (12) : 2049 - 2052
  • [32] 1,2-disubstituted ethylene in radical polymerization
    M. N. Gorbunova
    N. V. El’chishcheva
    Russian Journal of Applied Chemistry, 2013, 86 : 1581 - 1586
  • [33] 1,2-disubstituted cyclobutane carbocyclic nucleosides
    Santana, L
    Teijeira, M
    Teran, C
    Uriarte, E
    BULLETIN DES SOCIETES CHIMIQUES BELGES, 1997, 106 (04): : 227 - 228
  • [34] HYDRATION OF STEROIDAL 1,2-DISUBSTITUTED ETHYLENES
    SONDHEIMER, F
    NUSSIM, M
    JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (02): : 630 - &
  • [35] Improved Syntheses of 1,2-Disubstituted Ferrocenes
    Werner, Georg
    Butenschoen, Holger
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2017, (02) : 378 - 387
  • [36] FACILE SYNTHESIS OF 1,2-DISUBSTITUTED AZIRIDINES
    DEKIMPE, N
    VERHE, R
    DEBUYCK, L
    SCHAMP, N
    SYNTHETIC COMMUNICATIONS, 1975, 5 (04) : 269 - 274
  • [37] 1,2-disubstituted ferrocene Lewis acids
    Venkatasubbalah, K
    Patel, Y
    Cruz, M
    Zakharov, LN
    Kassel, S
    Rheingold, AL
    Jäkle, F
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U2218 - U2219
  • [38] A SIMPLE CONVERSION OF [E]- INTO THE ISOMERIC [Z]-2-(1-SUBSTITUTED-1-ALKENYL)-1,3,2-DIOXABORINANES, PROVIDING A CONVENIENT STEREOSPECIFIC SYNTHESIS OF BOTH [E]-1,2-DISUBSTITUTED AND [Z]-1,2-DISUBSTITUTED VINYL BROMIDES
    BROWN, HC
    BHAT, NG
    TETRAHEDRON LETTERS, 1988, 29 (01) : 21 - 24
  • [39] PREPARATION AND ABSORPTION SPECTRA OF 1,2-DISUBSTITUTED AND 2,3-DISUBSTITUTED DIBENZOTHIOPHENE DERIVATIVES
    SAWICKI, E
    JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (04): : 608 - 614
  • [40] SYNTHESIS OF 1,2-DISUBSTITUTED AND 1,7-DISUBSTITUTED PYRENES
    VANDENBRAKENVANLEERSUM, AM
    CORNELISSE, J
    LUGTENBURG, J
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (15) : 1156 - 1157
12345